Advice on putting together a decent portable setup

I've decided it's time to upgrade my gear, but the audiophile world is confusing to say the least. Being a broke teenager, I've made do with a pair of OMX 70s (or a borrowed set of SR 60s) and an iPod Touch 2g for what seems like an eternity, but it's time for a change.

I generally listen to music in the house or whilst walking about outside, so a bit of sound leakage (inwards) is actually desirable. I've tried a few pairs of over ear and in ear headphones, but most sound really bassy and muddy (even at with my usual Apple Lossless). So far, the headphones that have suited me best are the Philips Fidelio M1s, and its little brother the Downtowns. Even then, they both sound quite muddy, almost uncomfortable when listening to Radiohead's Amnesiac; among other albums. I was also quite dissapointed with Bose and Sony; being too mid biased and bassy respectively. Perhaps this is due to being used to such terrible, trebly headphones, or maybe it's my iPod's terrible EQ.

I've heard that an amp would help clear this up, but I don't want to spend £50 on a FiiO E11 unless it's going to make a noticable difference. To add another spanner to the works, I'm 15 so many over ear headphones are too big for me and look too ridiculous to leave the house in. In ear headphones also have their drawbacks as they don't stay in my ears and are often too bassy for my liking.

Could any of you guys offer some advice to help me out?
EDIT: My budget (for headphones) is about £40-60, but I'm leaning more towads the lower end
Thanks.

The Philips M1 that I had was so severely recessed in the treble that it was unfixable with iPod EQ, or anything else for that matter. But there are some good portable headphones that even if they aren't perfect, you can make them better for you with the EQ's that an iPod provides.

The Philips M1 that I had was so severely recessed in the treble that it was unfixable with iPod EQ, or anything else for that matter.

Click to expand...

The ones I tried weren't that bad, perhaps they've received some complaints and swapped the drivers out. They were quite bassy, but that can be EQ out. What really got to me was the lack of clarity. Maybe it's just a lack of high end (making them sound dull), or maybe it's the little internal amp in my iPod being pushed to its limit.

It's not the most elegant solution, but there's quite a few good EQ apps out there too. The Denon one's pretty good, although it saps battery life. TBH, the iPod presets are too extreme to be useful (I mainly stick it on Rock or Bass reducer and have done with it).

I actually tried those Sennheisers and I wasn't too impressed. IIRC, they lacked 'emotion' - they sounded a little dead to me. Then again, like the Fidelios, I had my iPod cranked to around 85% volume so their impedance is probably a bit too high to work without an amp. On a better system (a decent DAC and a PC), I recon they'd sound great, however.

I'm running at a loss here. IEMs seem to fit the bill as far as clarity and 'flatness' is concerned, but they block out a lot of sound and aren't as comfy. I think I might have to make a compromise - perhaps buying a set of cheap IEMs (E30s perhaps?) for cycling and pocketability, and a pair of over ears for listening pleasure.

What i'm really stuck on is the amps. Do they really make that much difference? Would buying one get rid of the muddiness or is my ancient iPod Touch 2g at fault?

Hmm, I guess it might be time for a new audio source. I know the law of diminishing returns plays a part, but I think my iPod might be the limiting factor here. It seems that as soon as I get above a certain price bracket, the sound quality doesn't improve.

I might see if I can try a those Fostex headphones - might be a change from the 'big brands'. As for the Grados, although they sound great, their ear cups are far too big for me. I'd look like an idiot wearing them, not to mention their shoddy cables.